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7 Holiday apartments & homes for a holiday with pool in Roccastrada

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Roccastrada

Casa Oliveto-Maremma

8 guests

150 m²

4 bedrooms

1 review

Very sustainable

Beautiful and family friendly holiday house with pool in a beautiful panoramic position. Sun terrace - children's playground - Large property -Top facility and equipment!

Very sustainable

from 281 € per night / night

5.0

prices from 281€ per night

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Roccastrada

Villa Melanie

6 guests

140 m²

3 bedrooms

1 review

Demanding holiday villa with pool in a fantastic location near the sea! Ideal for family or friends - 6 + 2

from 363 € per night / night

5.0

prices from 363€ per night

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Roccastrada

Casa Mauro with private pool

6 guests

54 m²

2 bedrooms (+1)

Holiday house for 2-4 pers. with pool

from 71 € per night / night

prices from 71€ per night

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Roccastrada

Casa Mauro with private pool

4 guests

50 m²

2 bedrooms

6 reviews

Holiday house for 2-4 pers. with pool

from 74 € per night / night

4.8

prices from 74€ per night

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Casa Carla mit Privat-Pool in Panorama-Alleinlage

Roccastrada

Casa Carla mit Privat-Pool in Panorama-Alleinlage

10 guests

130 m²

5 bedrooms

Holiday home Casa Carla with private pool, secluded location in Roccastrada, Tuscany, 130m² for up to 9 people.

from 207 € per night / night

prices from 207€ per night

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Orchideenfarm mit 3 Wohnungen und Pool bei Montemassi

Roccastrada

Orchideenfarm mit 3 Wohnungen und Pool bei Montemassi

4 guests

42 m²

1 bedroom

3 holiday apartments near Montemassi, each for 4 people, 42m², 1 bedroom, private terrace, pool.

from 61 € per night / night

prices from 61€ per night

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Roccastrada

Casa Mauro with private pool

9 guests

150 m²

4 bedrooms

Luxurious natural stone villa with large swimming pool 15 x 4 m x 1.30 m deep for 2 - 9 people.

from 533 € per night / night

prices from 534€ per night

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Accommodations near Roccastrada

These accommodations match your search but are located outside of the destination area.

4 km from Roccastrada

Sassofortino

Casa Pagiano

6 guests

75 m²

3 bedrooms

11 reviews

Apartment in the countryside 2-6 pers. 35 km sea

from 94 € per night / night

4.7

prices from 94€ per night

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5 km from Roccastrada

Sassofortino

Casa vista

5 guests

85 m²

2 bedrooms (+1)

Holiday home Casa Vista in Sassofortino, Tuscany with 85m² living space, 3 rooms, max 5 persons casa vista stands high above the Campo with a sweeping view down to the sea

from 367 € per night / night

prices from 367€ per night

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5 km from Roccastrada

Sassofortino

Casa Nuova

6 guests

120 m²

4 bedrooms

from 245 € per night / night

prices from 246€ per night

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6 km from Roccastrada

Roccatederighi

Scoiattolo + Riccio

4 guests

40 m²

2 bedrooms

Holiday house with pool for 2-4 pers

from 71 € per night / night

prices from 71€ per night

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7 km from Roccastrada

Montemassi

Casa Perete

4 guests

65 m²

3 bedrooms

1 review

Holiday home in a secluded location with private pool for 2-4 persons near Montemassi, Roccastrada-Tuscany near the sea

from 78 € per night / night

5.0

prices from 79€ per night

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7 km from Roccastrada

Roccatederighi

Casa Dora - privater Garten, Pool

5 guests

80 m²

3 bedrooms

from 60 € per night / night

prices from 60€ per night

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8 km from Roccastrada

Montemassi

Herrenhaus, Whg 45 m², Pool, Garten

6 guests

180 m²

3 bedrooms

Luxurious holiday home with private pool on the top of a hill with panoramic views all around for up to 6+1 children

from 425 € per night / night

prices from 426€ per night

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20%

9 km from Roccastrada

Grosseto

Ferienhaus mit eigenem Pool

8 guests

120 m²

4 bedrooms

1 review

Free cancellation

20% Promotion 06/30/2026 - 07/11/2026

Detached country house in the middle of nature, in the province of Grosseto, panoramic location, very large property (5 ha) with private pool, fireplace, wifi, TV, barbecue, fenced garden

Free cancellation

20% Promotion 06/30/2026 - 07/11/2026

from 235 € per night / night

5.0

prices from 236€ per night

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14 km from Roccastrada

Boccheggiano

Villa Lia

8 guests

140 m²

4 bedrooms

1 review

Free cancellation

Sustainable

Free cancellation

Sustainable

from 176 € per night / night

5.0

prices from 177€ per night

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15 km from Roccastrada

Ribolla

Casa Casteani with Pool

5 guests

80 m²

2 bedrooms

2 reviews

2 Apts. with pool for 4-12 pers. 22 km to the sea

from 105 € per night / night

4.9

prices from 106€ per night

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47%

16 km from Roccastrada

Grosseto

Romantic holiday home with pool

4 guests

85 m²

2 bedrooms

1 review

47% Promotion 06/30/2026 - 07/06/2026

Rustic country house, fenced garden with pool, completely private - no other people, close to the wide natural beaches of Alberese and Marina di Grosseto, built-in barbecue, WIFI

47% Promotion 06/30/2026 - 07/06/2026

from 207 € per night / night

4.6

prices from 207€ per night

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17 km from Roccastrada

Montepescali

La Torre mit Privat-Pool

5 guests

64 m²

2 bedrooms (+1)

Medieval residential tower of a former city wall, large saltwater pool, spectacular view!

from 141 € per night / night

prices from 141€ per night

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17 km from Roccastrada

Massa Marittima

Villa with panoramic view and pool

6 guests

120 m²

4 bedrooms

- Comfortable stone house, finished in 2017 - Absolute peace, absolute peace in nature, wonderful view - Pool directly in front of the house, 30 minutes to the sea -

from 184 € per night / night

prices from 184€ per night

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18 km from Roccastrada

Gavorrano

Loft-Haus Fienile

6 guests

100 m²

2 bedrooms

Loft house 100 m² huge fireplace, living/TV area, sofa bed, sleeping area round beds 210 cm Dm, kitchen, spacious bathroom with shower, roman bathtub, bidet, WC

from 102 € per night / night

prices from 102€ per night

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18 km from Roccastrada

Gavorrano

Casina Piccola

4 guests

37 m²

1 bedroom (+1)

Sustainable

Loft house 100 m² huge fireplace, living/TV area, sofa bed, sleeping area round beds 210 cm Dm, kitchen, spacious bathroom with shower, roman bathtub, bidet, WC

Sustainable

from 65 € per night / night

prices from 65€ per night

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Guest reviews of our holiday apartments in Roccastrada

4.6

Casa Mauro with private pool

Roccastrada

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Casa Mauro Beautiful cottage in a secluded location

Nice small, cosy cottage in a secluded location. Very beautiful view of the Maremma plain. The house is clean and attractively furnished. Everything you need is on site. The pool is perfectly adequate and is cleaned daily by Mauro, the landlord
Mauro and his wife are very lovely people, and always provided us with fresh vegetables from their own garden.
It was a dream for our two dogs, as the large property is completely surrounded by a sturdy, 1.80 high fence. There is also a pine forest on the property, which provides enough shade for the four-legged friends in the midday heat.
The access to the cottage is via a dirt road, let's say in need of renovation, which is unsuitable for sports cars, but perfectly passable with a normal car.
It is advisable to bring enough mosquito repellent. The windows of the house have fly screens, which are also "tight", but the little pests always find a way into the house somehow.
The neighbours, too, be it the locals or the other holiday home residents (all at a sufficient distance), are a funny bunch. They are always ready for a quick chat at the fence or a glass of red wine as they pass by. Caution: The homemade wine has a lot to offer
3 glasses and you sleep peacefully - despite the mosquitoes ????.
Conclusion: We will be back.

from 74€ night

5.0

Casa Oliveto-Maremma

Roccastrada

View German

Wonderful vacation in the Maremma

We were at the Oliveto holiday home at the end of May with 4 people. We really liked the vacation. We were lucky that the owner was there and showed us everything. That was naturally very positive. The directions were good - we found the house right away. Since no one had been in the house before us and the owner had just prepared it, everything was very clean and the garden was tip-top, as well as the pool. The impression of the house and garden is great. The furnishings are very high quality. We can only recommend the house with the best memories. The house is also great for children! There is a very large garden with football goals and a trampoline. Restaurant recommendations are available in the house. Many thanks to Mrs. Schuler for the mediation and greetings to the owner!

from 281€ night

5.0

Verified guest from Tourist-paradise.com

Villa Melanie

Roccastrada

View German

A wonderful vacation

Comment: We spent a very relaxing week of vacation at Villa Melanie. The holiday house is somewhat secluded. However, this provides a lot of privacy, which is very pleasant. With a car, you can quickly reach all the sights. It is also not far to go shopping and to the sea. Everything is very clean and well-maintained. Once a week, the gardener comes and cleans the pool. The equipment leaves nothing to be desired. Everything you need is available. The landlord is very friendly and can always be reached by phone in case of a problem. We would like to take this opportunity to thank Marco and his wife once again for this relaxing week of vacation. We will definitely come back. Frank, Michaela, and Elisa Schulz.

from 363€ night